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A Sustainable Synthesis of Asymmetric Phenazines and Phenoxazinones Mediated by CotA‐Laccase
Author(s) -
Sousa Ana Catarina,
Conceição Oliveira M.,
Martins Lígia O.,
Robalo M. Paula
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701228
Subject(s) - chemistry , aromatization , intramolecular force , substrate (aquarium) , combinatorial chemistry , nucleophile , laccase , nucleophilic aromatic substitution , enantioselective synthesis , nucleophilic substitution , organic chemistry , catalysis , enzyme , oceanography , geology
An efficient and sustainable one‐step procedure for the synthesis of new asymmetric phenazines and phenoxazinones from commercially available ortho ‐substituted diamines and ortho ‐substituted hydroxyamines is reported. In this study we have expanded the substrate scope of CotA‐laccase‐catalyzed aerobic oxidations through the use of aromatic amines presenting variable functional groups, including N ‐substitution, contributing to the rational synthesis of different heterocyclic scaffolds. The transformations proceed smoothly through a cascade of oxidative reactions to the benzoquinonediimine intermediates followed by nucleophilic addition, intramolecular cyclization and aromatization, all performed in mild conditions.